How do you train the trainers to be exceptional leaders?
In this episode, we chat with Jonathan Kroll, PhD, Founder and Executive Director of Leadership Trainer. Jonathan shares the journey of his organization, from its beginnings in Nicaragua to its expansion in the U.S., and their mission to transform leadership education through innovative programs and hands-on, experiential learning.
Jonathan dives deep into the common pitfalls of leadership development and how Leadership Trainer is addressing these gaps to ensure trainers are not just prepared, but exceptional in their roles. He also offers valuable advice on discipline, persistence, and focus in nonprofit leadership.
Get involved with Leadership Trainer and learn more at leadershiptrainer.org. You can also find Jonathan’s book, Preparing Leadership Educators, on Amazon.
Stephanie:
Hi, Jonathan. How are you?
Jonathan:
I’m doing great. Thank you so much.
And thank you for having me on the Nonprofit Therapy podcast.
Stephanie:
Thank you for being here!
Today, we have Jonathan Kroll, the leader of Leadership Trainer, an amazing organization.
He’s a master trainer, a leadership educator, and an award-winning author — and we’ll get into the book later!
For now, let’s dive in.
Tell us a little bit about your amazing organization and how you’re transforming the leadership training landscape.
Jonathan:
Yes! Well, we’re definitely transforming leadership training by focusing on trainer and facilitator preparation.
We’ve all sat through boring, lecture-style, slide-deck presentations — and not only are they boring, they’re ineffective for learning and applying knowledge.
At Leadership Trainer, we focus on ensuring the next generation of leaders can effectively navigate the challenges they’ll inevitably face — by preparing today’s trainers to consistently deliver high-impact, high-engagement, high-enjoyment sessions that actually lead to learning and real-world application.
In short, we help people stop doing terrible trainings and create transformative experiences instead.
Stephanie:
Amazing!
And by the way, congratulations — it was just your eight-year anniversary, right?
Jonathan:
Yes — two days ago!
Stephanie:
Wow! Congratulations. Eight years is definitely a milestone!
Jonathan:
Thank you.
We’re really excited to have that kind of longevity.
We actually started doing this work in Nicaragua, after about a decade of me volunteering independently in leadership development.
Friends and colleagues kept saying, Jonathan, teach us how you do this! — because they were still stuck in that boring lecture-style training.
So I created our Leadership Trainer Certification Program, giving them the knowledge, skills, tools, and resources to consistently facilitate amazing trainings.
And then in 2018, due to political unrest in Nicaragua, I returned to the U.S. — Boston, where I’m from — and we restructured for professional audiences: nonprofit leaders, university admins, government personnel, corporate trainers.
Stephanie:
That’s crazy — so it all started in Nicaragua!
Tell us more about how you first got there and what inspired the initiative.
Jonathan:
In 2005, I was an independent English language volunteer.
Through a mentor, I met a Nicaraguan couple who had founded a language center, and I wanted to go somewhere in the world and do something meaningful.
So I spent six months there teaching English — and ended up facilitating leadership programs too.
I completely fell in love with the place and the people.
From 2005 to 2015, I kept going back — one, two, sometimes three times a year — facilitating leadership training for university students, local community leaders, business executives, all kinds of groups.
Stephanie:
¡Hablas español?
Jonathan:
¡Sí! (Laughs)
It was an incredible experience.
Later, after earning my doctorate in leadership, I wanted to expand the impact and felt a nonprofit structure was the best way to do it.
That’s how Leadership Trainer was born.
Stephanie:
Incredible.
And somewhere along this journey, you also became an award-winning author!
When did the book come into the picture?
Jonathan:
Yes!
The book, Preparing Leadership Educators, actually started as our training manual for the certification program in Nicaragua.
At the time, there were very few leadership education books written or translated into Spanish — so I wrote a resource that covered leadership theory, practice, and facilitation.
The first version was in English.
We had former participants help us translate it into Spanish — but then, because of the unrest, we had to pause that work.
When I returned to the U.S., I realized — this could be a full book.
I spent about a year and a half turning it into a real book, connected with a publisher, and it’s now available wherever books are sold.
It’s won awards, been nominated for others, and it’s our course text for the certification program today.
Stephanie:
That’s amazing.
And your website — wow, it’s packed!
You offer so many programs and resources.
Can you walk us through some of them?
Jonathan:
Sure!
Our flagship is the Leadership Trainer Certification Program — an immersive, three-and-a-half-day retreat (or hybrid with a virtual piece).
We also do onsite training for organizations.
Then there’s the Mastery Course — a self-paced online course with over four hours of video content and a 140-page manual.
We offer coaching, consulting for leadership programs — the whole range.
Stephanie:
Totally.
Now — we’re talking about training the trainer, right?
Because strong trainers create strong futures.
How do you think strong leadership really transforms communities and organizations?
Jonathan:
We know that ineffective leadership creates massive challenges — or makes existing challenges worse.
Leadership development is a billion-dollar industry — and yet so much training doesn’t really work.
Why? Because many trainers don’t know how to facilitate learning effectively.
We tend to default to what’s comfortable — boring lectures — instead of engaging, experiential, reflective facilitation.
That’s what we teach: how to create deep learning experiences that actually translate into practice.
Stephanie:
Makes total sense.
Now, because this podcast is called Nonprofit Therapy — we know running a nonprofit isn’t easy!
What’s a challenge you’ve faced — and maybe a tip you’d give other nonprofit leaders?
Jonathan:
Two words: discipline and persistence.
Leading a nonprofit requires both.
You have to stay disciplined — focused on your mission, your core work — and persistent, because challenges will come.
It’s about keeping at it even when it’s hard.
Stephanie:
By the way, I really hear the enthusiasm in your voice when you talk about this.
It’s clear you live your own advice.
Jonathan:
Thank you!
Discipline and persistence are critical leadership traits — not just for nonprofits, but everywhere.
Stephanie:
You heard him, everyone — persistence and discipline. Noted!
Jonathan:
(Laughs) Yes!
Stephanie:
You’ve been with Vee for quite a while — I think even one of our first customers!
Can you share a little about how Vee has supported your mission?
Jonathan:
Absolutely.
We’ve loved working with Vee.
First, on the social media side: when our part-time social media coordinator stepped away, Vee filled that gap beautifully — creating posts that feel authentic, aligned, and professional.
Second, on grants: Vee has been consistently sending us two, three, sometimes four grant opportunities a week that align with our mission.
It’s been an incredible partnership.
Stephanie:
So happy to hear that.
That’s exactly what we aim to do — support leaders like you so you can stay focused on changing the world.
Jonathan:
You’re doing a phenomenal job. Thank you!
Stephanie:
Thank you, Jonathan.
To wrap up — where can listeners find you, your programs, and your book?
Jonathan:
You can visit leadershiptrainer.org.
If you or someone you know facilitates trainings — and wants to transition from terrible trainings to transformational experiences — we’d love to connect.
My book, Preparing Leadership Educators, is available on Amazon and through our website as well.
Stephanie:
Amazing.
Thank you so much for being here, Jonathan.
It was great to have you on Nonprofit Therapy.
Until next time!
Jonathan:
Thank you! Take care.
